Hillary Chybinski: What to Wear: Weddings, Cocktail Parties and Events

Wednesday, October 19, 2016

What to Wear: Weddings, Cocktail Parties and Events

Ideas and Inspiration for what to wear to weddings, cocktail parties and special events.
It's been years since I've had to get "dressed up." Don't get me wrong, I've worn dresses and gone to events and parties, but nothing that really required a new purchase, serious thought to accessories and just the right fancy heels. But all that changed when I had a Cocktail Attire dinner in NYC and a Family Wedding, both in the same week. Shopping Powers - activate!

I must have picked the worst week of the year to shop, because while I looked at a TON of dresses, everything was WRONG: too dressy, too "young", too "old" or just plain old too ugly! Can you feel me? As desperation began to set in, I made a last ditch trip to the mall, dragging both boys with me (I KNOW - crazy!) I went into the dress shop at Bloomingdales and my heart started to sink. Everything looked like a boring work dress or a dress fit for a beauty pageant (I like a little bling, but come on!) WHERE were all the dresses "normal" people wear?

I started pulling dresses off the rack to try on, after all the kids were waiting for me, while recommending the ugliest dresses to try on. I tried on eight and settled on one: a pretty green Ralph Lauren that would be perfect for an afternoon wedding at a ranch. I had a vision of a green dress when the save the date card came, but I never thought I'd actually find one.

Green Ralph Lauren Cocktail Dress - perfect for an afternoon wedding

Loving my green dress, I suddenly came to the realization that while it was the PERFECT afternoon wedding dress, it didn't feel dressy enough for a fancy dinner at the gorgeous Waldorf Astoria in NYC. I needed a LBD - stat!

My go-to "occasion" store of the moment is Ann Taylor, and has been for years. They did not let me down. I found the perfect, modern LBD at a great price besides! In a hat tip to modern technology, I first spotted the dress in my weekly email from AT, and decided to take a run to my nearest shop to try it on. I fluctuate in dress sizes because if it fits my chest, it's typically too large in the hips and vice versa. So the first dress I tired on fit, but seemed a little "off". I ended up trying a size down and it looked MUCH better. Sometimes you have to try on a few of the same dress to find the right fit.

The classic Little BLack Dress - a wardrobe staple

A Little Black Dress, Classic Patent Pumps, and a wrap are perfect for a night out

Some ideas when the invitation calls for dressy:

A Little Black Dress. This is a classic for a reason: it works. The key is finding one that works with YOUR body. I did a quick Pinterest search for ideas, and I went with a simple shift design in a stretchy fabric. I kept my accessories simple as well.

Try a jumpsuit. I would never in a million years think this would work for me, but I saw a few at the dinner I went to, and I've recently seen some friends post pictures wearing them, so I think they can be a great choice!

Try on a lot of dresses. Take some dresses that fit your style into the dressing room and TRY THEM ON. That ugly dress on the hangar could easily turn out to be THE ONE on your actual body. It's hard, I know, but seriously, you need to try them on.

Expand your style options. While you are trying on dresses, don't be afraid to try something "different" than your usual style. The blousey top and fuller skirt on the green dress, were not my typical style, but they helped to hide some of my less favorite body parts.

A Little Black Dress is perfect for a night out with Mickey Mouse

So don't panic when that invitation shows up. There are some great choices out there for women of all ages and sizes. Pick something that looks great ON YOU, because you will have the best time in something that you know looks great and that you feel comfortable in.

A bright color cocktail dress is a great option for an afternoon wedding

What's the last dressy thing you bought or found? What made it such a stand out?

catch you soon -
This post is linked up at The Pleated Poppy - be sure to check it out for even more outfit ideas and inspiration.

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